85026-06-8

Basic information

• Product Name: erythro-2-hydroxy-3-methylbutane-1,4-dioic acid
• CAS NO: 85026-06-8
• Molecular Weight: 148.116
• Mol File: 85026-06-8.mol

Chemical Properties

• CAS DataBase Reference: erythro-2-hydroxy-3-methylbutane-1,4-dioic acid(CAS DataBase Reference)
• NIST Chemistry Reference: erythro-2-hydroxy-3-methylbutane-1,4-dioic acid(85026-06-8)
• EPA Substance Registry System: erythro-2-hydroxy-3-methylbutane-1,4-dioic acid(85026-06-8)

Safety Data

• Hazardous Substances Data: 85026-06-8(Hazardous Substances Data)

Upstream product

• 100806-42-6 (E)-(2S,3S)-3-Hydroxy-2-methyl-hex-4-enoic acid 
• 113564-09-3 (E,2R^*,3S^*)-3-hydroxy-2-methyl-4-hexenoic acid 
• 93504-92-8 2-hydroxy-3-methylbutanedioic acid diethyl ester 
• 63921-06-2 3-methyl-2-oxo-butane-1,4-dioic acid dimethyl ester 
• 759-65-9 diethyl oxalpropionate 
• 642-92-2 D,L-threo-β-methylaspartic acid 
• 50460-80-5 (2S,3R)-2-Hydroxy-3-methylbernsteinsaeure-dimethylester 
• 874646-33-0 diisopropyl (2R,3S)-2-methyl-3-hydroxybutanedioate 
• 73840-71-8 diethyl (2S,3R)-(+)-2-hydroxy-3-methylsuccinate 

Downstream Products

• 85199-56-0 2-Methyl-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-succinic acid dimethyl ester 
• 89497-03-0 (2R,3R)-2-Methyl-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-succinic acid dimethyl ester 
• 85249-22-5 (2S,3R)-2-Methyl-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-succinic acid dimethyl ester 
• 50460-80-5 dimethyl 2-hydroxy-3-methylbutane-1,4-dioate 
• 50460-80-5 dimethyl 2-hydroxy-3-methylbutane-1,4-dioate 
• 50460-80-5 (2S,3R)-2-Hydroxy-3-methylbernsteinsaeure-dimethylester 
• 5380-37-0 (2S,3R)-2-Hydroxy-3-methyl-succinic acid 
• 5380-36-9 (+)-erythro-3-Methylaepfelsaeure 
• 5380-36-9 (-)-threo-3-Methylaepfelsaeure 
• 5380-37-0 (2S,3S)-2-Hydroxy-3-methyl-succinic acid 
• 111833-04-6 (2S,3S)-2-Acetoxy-4-benzyloxy-3-methyl-butyric acid methyl ester 
• 111833-00-2 (2S,3S)-4-benzyloxy-2-hydroxy-3-methylbuttersaeure 

Relevant articles and documents

The sex pheromone of the wasp spider Argiope bruennichi

(Figure Presented) Wasp spider looking for a mate: Female wasp spiders (see picture) use trimethyl methylcitrate as a volatile cue to attract males. The experiments were performed on a sunny meadow, showing for the first time that spider traps can be used to trap spiders in the field (photo: Helen Sandford).

N-HYDROXYAMIDE DERIVATIVES AND USE THEREOF

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On the Stereochemistry of E'- and E''-Reactions

The decarboxylative E'-dehydration of β,γ-unsaturated δ-hydroxy acids with DMF-dineopentylacetal shows SYN-faciality irrespective of whether the conformation of the hydroxy group relative to the double bond axis is anticlinal or synclinal.

Electrochemical Oxidation of (S)-Malic-Acid Derivatives: a Route to Enantiomerically Pure Alkylmalonaldehydic Esters

The 3,3-dialkylmalic-acid diesters, prepared by the previously described diastereoselective alkylations through dilithium alkoxide enolates, are saponified to the monoesters containing a free α-hydroxycarboxylic-acid moiety.The monoesters are subjected to electrochemical oxidative decarboxylation in MeOH.If the intermediate monoacids are purified, the malonaldehydic esters (2-formyl-2-alkoxycarboxylates) obtained by this procedure are enantiomerically pure; they have the same structural features, i.e. two enantiotopic functionalized branches on the (persubstituted) stereogenic center, as the well known 3-hydroxy-2-methylpropanoic acid ('Roche acid') which was employed frequently as a starting material for the preparation of either enantiomer of various target molecules.

Synthesis of erythro-2-Hydroxy-3-methylbutane-1,4-dioic Acid

Reduction of ethyl 3-methyl-2-oxobutane-1,4-dioate (3) with sodium borohydride furnishes a 6:1 mixture of ethyl erythro-2-hydroxy-3-methylbutane-1,4-dioate (8) and ethyl threo-2-hydroxy-3-methylbutane-1,4-dioate (18).Hydrolysis of this mixture with aq. hydrochloric acid gives a mixture of acids from which pure erythro-2-hydroxy-3-methylbutane-1,4-dioic acid (4) has been isolated.The stereochemistry of 4 has been establishrd by PMR and by transforming it to the anhydride, erythro-dihydro-3-acetyloxy-4-methyl-2,5-furandione (26).

The Use of Microorganisms in Organic Synthesis. II. Microbiological Asymmetric Reduction of 2-Methyl-3-oxosuccinates

In order to synthesize four optically active methyl 2-methylmalates (10-13), microbiological asymmetric reduction of the corresponding dimethyl 2-methyl-3-oxosuccinate (9) was carried out.The β-keto diester 9 was found to be reduced by fermenting baker's yeast (Saccharomyces cerevisiae) and Candida albicans to afford a mixture of the (2R,3R)-isomer 10 and the (2S,3R)-isomer 11.Although the optical purity of 10 produced by Candida albicans was reasonably high (95percent e.e.), optical yields of other products were unexpectedly low.However, identification of the four possible isomers 14-17 was found to be easily carried out by means of nuclear magnetic resonance spectroscopy.Keywords - α-methyl-β-keto ester; methylmalate; asymmetric reduction; microbiological reduction; yeast; methyl 2-methylmalate